138622

D-(−)-Chinasäure

98%

• Synonym(e): (-)-Quinic acid, (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid, D-(-)-Quinic acid
• Empirische Formel (Hill-System): C₇H₁₂O₆
• CAS-Nummer: 77-95-2
• Molekulargewicht: 192.17
• Beilstein: 2212412
• EG-Nummer: 201-072-8
• MDL-Nummer: MFCD00003864
• UNSPSC-Code: 51113400
• PubChem Substanz-ID: 24848361
• NACRES: NA.22

Eigenschaften

• Assay: 98%
• Form: powder
• Optische Aktivität: [α]20/D −43.9°, c = 11.2 in H₂O
• SMILES String: O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
• InChI: 1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
• InChIKey: AAWZDTNXLSGCEK-WYWMIBKRSA-N

Beschreibung

Allgemeine Beschreibung

D-(-)-Quinic acid, a plant metabolite, is chiral building block used in multistep chemical synthesis of natural compounds.

Anwendung

D-(−)-Quinic acid can be used as:      

• A chiral selector electrolyte along with copper(II) sulfate. This electrolyte is utilized in chiral resolution DL-tartaric acid by ligand-exchange capillary electrophoresis method.        
• A starting material in the synthesis of stereoisomers of 3,4,6-trihydroxyazepanes, 7-hydroxymethyl-3,4,5-trihydroxyazepanes, and 3,4,5-trihydroxyazepanes, as potential inhibitors of glycosidase.        
• A precursor for the preparation of trihydroxy piperidine derivatives and (+)-proto-quercitol glycosidase inhibitors.

D-(-)-Quinic acid has been used as a standard to determine the composition of organic acids in bitter gentian teas and in developing cranberry fruit by HPLC. It may be used in the preparation of 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H319
• P-Sätze: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Gefahreneinstufungen: Eye Irrit. 2
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 1
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)